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Hydrochloric Acid → HCID 17816478, compound

HRID 2249697
Notes
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Reaction equation

HRID 2249697 reaction equation
[Br:1][C:2]1[C:10]2[NH:9][C:8](=[O:11])[NH:7][C:6]=2[CH:5]=[C:4]([Br:12])[C:3]=1[C:13]([O:15][CH3:16])=[O:14].[H-].[Na+].[CH2:19](Br)[CH2:20][CH:21]([CH3:23])[CH3:22].Cl>CN(C)C=O.O.C(OCC)(=O)C>[Br:1][C:2]1[C:10]2[N:9]([CH2:19][CH2:20][CH:21]([CH3:23])[CH3:22])[C:8](=[O:11])[N:7]([CH2:10][CH2:2][CH:3]([CH3:13])[CH3:4])[C:6]=2[CH:5]=[C:4]([Br:12])[C:3]=1[C:13]([O:15][CH3:16])=[O:14]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 78911-Bromo-3-methylbutaneHCID 24758Sodium hydrideHCID 17816488HCID 17816488, compound

Product 1

HCID 17816478HCID 17816478, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent
HCID 6228
Dimethylformamide
Solvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
55 °C

Procedure

In 10 ml of N,N-dimethylformamide are suspended 0.95 g of methyl 4,6-dibromo-2-oxo-2,3-dihydro-1H-benzimidazole-5-carboxylate, 0.24 g of 60% sodium hydride and 0.7 ml of isopentyl bromide. The suspension is stirred at 50-60° C. for 3 hours. The reaction mixture is added to a mixture of ethyl acetate and water, pH is adjusted to 2 with 2 mol/L hydrochloric acid, and the organic layer is separated. The organic layer thus obtained is washed with water and saturated aqueous solution of sodium chloride successively and dried over anhydrous magnesium sulfate, and then the solvent is distilled off under reduced pressure. Thus, 0.71 g of methyl 4,6-dibromo-1,3-diisopentyl-2-oxo-2,3-dihydro-1H-benzimidazole-5-carboxylate is obtained as a light brown-colored solid product.

Workup

  1. customthe organic layer is separated
  2. customThe organic layer thus obtained
  3. washis washed with water and saturated aqueous solution of sodium chloride successively
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent is distilled off under reduced pressure

Sources & evidence

ORD record
ord-8be4fc6a151945349a1ce116a9ce0165
Source dataset
uspto-grants-2008_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07314888B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes